Hydrochloric Acid → HCID 86714702, compound

HRID 529218Notes

Reaction equation

HRID 529218 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:12]([OH:14])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:26]([O:33][C:34](=[O:48])[C@H:35]([CH2:37][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[NH2:36])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl>ClCCl>[CH2:26]([O:33][C:34](=[O:48])[C@H:35]([CH2:37][C:38]([O:40][CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)=[O:39])[NH:36][C:12]([C:9]1([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:10][CH2:11]1)=[O:14])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2808531L-Aspartic acid, 1,4-bis(phenylmethyl) ester, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 86714702HCID 86714702, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)aminocyclopropanecarboxylic acid (257 mg, 1.28 mmol), L-aspartic acid dibenzyl ester tosylate (806 mg, 1.66 mmol), WSC hydrochloride (367 mg, 1.92 mmol), and 1-hydroxybenzotriazole (291 mg, 1.92 mmol) in dichloromethane (4.0 ml) was added N,N-diisopropylethylamine (1.30 mL, 7.66 mmol), and the mixture was stirred at room temperature for 7 hours. 1N Hydrochloric acid was added to the reaction mixture, the mixture was extracted 3 times with dichloromethane, and the obtained dichloromethane layer was washed with saturated brine. After drying over anhydrous magnesium sulfate, the desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (598 mg, 1.20 mmol, 94%).

Workup

  1. extractionthe mixture was extracted 3 times with dichloromethane
  2. washthe obtained dichloromethane layer was washed with saturated brine
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationthe desiccant was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9c595e362c6f4cb19f9bc0c084100e01
Source dataset
uspto-grants-2016_05
Patent number
US09346821B2

Reaction notes

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